The glycoluril compound is a heterocyclic compound having four urea nitrogens in the ring structure thereof, and is widely used as a raw material in the production of various substances and a component of drugs in various applications, by utilizing the reactivity of the urea nitrogen.
For example, it is known that the glycoluril compound is allowed to react with an aldehyde such as dimethoxyethanal to produce an amino plastic resin and the resultant is used as a crosslinking agent for cellulose (see Patent Document 1).
It is also known that an emulsion containing a copolymer of vinyl acetate, ethylene and a self-crosslinkable monomer, and a tetramethylol glycoluril compound is used as a binder for a non-woven fabric (see Patent Document 2).
It is further known to use the compound as a crosslinking agent for fixing a polyhexamethylene biguanide compound, which is a water-soluble polymer antimicrobial agent, to a fiber (see Patent Document 3).
Compounds having a plurality of high-reactive allyl groups in the molecule, for example, triallylisocyanurate, are widely employed as a crosslinking agent for synthetic resin or synthetic rubber. Tetraallylglycoluril compounds, which function similar to the triallylisocyanurate, are also known (see Patent Document 4).
On the other hand, compounds having a plurality of thiol groups in the molecule are also well-known as a curing agent for an epoxy resin. For example, an epoxy resin composition containing a polythiol compound used as a curing agent and a reaction product of an amine with an epoxy compound as a curing accelerator is proposed. It is said that the epoxy resin composition has a long working life and is quickly cured at a relatively low temperature (see Patent Document 5).
An epoxy resin composition containing, as a curing accelerator, a reaction product of an isocyanate compound with a compound having at least one primary and/or secondary amino group in the molecule is also proposed. It is said that the epoxy resin composition also has a long working life and is excellent in curability (see Patent Document 6).
In addition, tris(3-mercaptopropyl)isocyanurate, which is also called trithiol isocyanurate, is proposed as a curing agent capable of providing a cured product of epoxy resin excellent in water resistance, because it has no ester group in the molecule (see Patent Document 7).